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10-Step, Gram-Scale Total Synthesis of (-)-Bipinnatin J.

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A concise and scalable total synthesis of (-)-bipinnatin J was achieved. This marine diterpenoid synthesis utilized novel Ni-electrocatalytic methods and unique synthetic sequences for efficient construction.

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Area of Science:

  • Organic Chemistry
  • Total Synthesis
  • Natural Products Chemistry

Background:

  • (-)-Bipinnatin J is a complex marine diterpenoid.
  • Efficient and scalable synthetic routes are needed for complex natural products.

Purpose of the Study:

  • To disclose a concise and scalable total synthesis of (-)-bipinnatin J.
  • To develop novel synthetic methodologies for complex diterpenoid construction.

Main Methods:

  • Convergent synthesis strategy.
  • Nickel-electrocatalytic decarboxylative cross-coupling using succinate.
  • Halogen dance-Zweifel sequence for trisubstituted furan synthesis.
  • Nickel-mediated 1,6-conjugate addition.
  • Asymmetric proton transfer.

Main Results:

  • Successful total synthesis of (-)-bipinnatin J from inexpensive starting materials.
  • Demonstrated scalability of the synthetic route.
  • Established the utility of Ni-electrocatalysis and novel sequences in complex molecule synthesis.

Conclusions:

  • The developed synthetic route is concise, scalable, and efficient.
  • The methodology provides a valuable platform for accessing related marine diterpenoids.
  • This work advances the field of natural product total synthesis.